


Dumbasses Date Dumbasses

by bloodscout



Category: Supernatural
Genre: Alternate Universe - High School, High School, M/M, POV Outsider, Prompt Fic
Language: English
Status: Completed
Published: 2012-11-30
Updated: 2012-11-30
Packaged: 2017-11-19 22:36:43
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,070
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/578359
Author URL: https://archiveofourown.org/users/bloodscout/pseuds/bloodscout
Summary: <blockquote class="userstuff">
              <p>Anna Milton wakes up every morning, knowing she can get any guy she wants</p>
            </blockquote>





	Dumbasses Date Dumbasses

**Author's Note:**

> Thanks to Michelle for the prompt!  
> I really don't hate Anna as much as this fic implies.

Anna Milton wakes up at 7am in the morning, washes off her night-time face mask, takes a shower, puts on her makeup and gets dressed. If she feels like it, she will have breakfast, but if not, she gets in her car and drives her brother to school.  
She does not, contrary to popular belief, eat anyone’s soul for breakfast, and she does not sew her clothes out of the curshed dreams of other teenage girls. She just wakes up this pretty, okay?  
The rumors are true, however, that Anna Milton wakes up every morning with the knowledge that she could have her pick of all the boys in school; the array of chocolates and flowers that arrived at her door every Valentine’s Day.  
Currently, she has her eyes set on a certain Dean Winchester. Dean is captain of the softball team, and he’s gorgeous. Not as gorgeous as Anna, but he’s high-school hot, at the very least. As she smacks her lips at her reflection, Anna tells herself that Dean is going to ask her out at her annual halloween party. There’s going to be alcohol, and dancing, and apple bobbing, so she rationalises that he really doesn’t have an excuse not to.  
Anna hears a sharp knock on her door, which could only be Castiel.  
‘Come in,’ she calls.  
Castiel opens the door with a quietness that must have skipped her other brothers.  
‘Hello, Anna,’ he says.  
‘Hello, Castiel,’ Anna replies, exasperation obvious in her tone. ‘What do you want?’ She hopes this will not be a repeat of when they were thirteen. Cas was just coming out, and he had asked Anna how to apply makeup, in the most awkward and confused way possible. It was the most mortifying two hours of the twins’ lives.  
‘I was just ensuring that the halloween party was still happening this year.’ he says, and it’s more of a statement than a question.  
‘Yeah, dumbass, like it is every year.’ She reaches for the curler and flicks it on.  
Castiel makes a small noise, maybe of concession, maybe of disappointment; Anna can never tell. Castiel is just as much of an enigma to her as he is to the rest of the student body.  
‘Be down at the car in 5, Cas!’ she calls to the sound of retreating footsteps.  
~~~  
Dean is leaning up against his car, talking to Cassie, Sam and Gabriel. Anna saunters over to them, invitations in hand. From the slam of the car door, she can tell Cas has followed her too.  
‘Hey!’ Dean shouts at her, and waves.  
Anna waves back, but so does Castiel. She shoots him a quick glare, and the slight smile drops of his face.  
‘Yes, of course, he was waving to you.’ Castiel mutters, not quite soft enough to slip past Anna’s attention.  
Anna takes the spot next to Dean, leaning her hip onto Dean’s car. It’s glossy and black and will probably look really great when Dean picks her up for their dates. She smiles at the group, liploss shining in the sun.  
‘Hey, Cas,’ Dean says as the other Milton arrives. Anna doesn’t mind that he’s agknowledging Cas - he’s probably just ebing nice.  
‘Hi guys,’ she says. She looks over to Dean, makes sure she has full eye contact. ‘Hi Dean.’  
Cassie rolls her eyes. ‘I’m off guys, see you in Chem, Sam.’ she announces, and leaves. Bitch.  
‘Good morning, sister.’ Gabriel greets, a little bitter. He’s tucked under Sam’s arm, leaning on Gabriel’s own car. ‘Going hunting, are we?’  
Anna ignores him, and addresses Dean instead. ‘So I know you go to our halloween party every year - let’s face it, everyone does,’  
Dean lets out a little chuckle. Anna smiles sweetly, glad that he’s amused. Then, Gabriel giggles, and Sam snorts, burying his nose in his boyfriend’s hair. Anna frowns a little, but relaxes her forehead as soon as she realises what he’s doing - there’s nothing attractiveabout frown lines - and follows their line of sight.  
Castiel is sitting cross legged on the footpath, a bird hopping back and forth in front of his outstreached hand. He is completely concentrating on the animal in front of him, almost willing it into his palm. Anna wants to scowl, but Castiel probably wouldn’t see it.  
‘Well,’ she interrupts. It’s loud enough to startle Dean back into notcing her, and it’s almost like he didn’t know she was there. Gabriel giggles again, and Anna remembers again why he’s her least favourite brother. At least Castiel is quiet.  
‘Well?’ Dean prompts, urging her to get on with it.  
‘The party’s on Saturday.’ she leans in a little, effectively cutting Gabriel and Sam off from the conversation. ‘I’d love it if you could come.’  
Dean nods, a little perplexed. ‘I was going to be there anyway, Anna.’  
Anna tilts her head to the side - it’s really the only similarity she has with Cas, that head tilt. She’s still pretty close into Dean’s personal space. ‘I just wanted to make sure you got a special invitation.’  
Dean’s eyebrows raise in what could be construed as interest.  
‘ A “special invitation”?’ Sam interrupts, wiggling his fingers in an approximation of air quotes. ‘Is that anything like what Gabriel gave me last night?’ he chuckles. Obviously Gabriel was dating the taller Winchester for his juvenile sense of humour.  
‘Gross, man.’ Dean complains. He turns back to Anna. ‘See you ‘round, Anna.’  
Anna smiles, and walks off to her locker, but not without glaring at Castiel on the way.  
~~~  
Anna was never one for the cheer squad - it was too preppy for her liking - but she turned up with the cheer squad to watch the softball team practice. She takes a seat next to the drink bottles, and waits for Dean to finish his play. When he comes over to get a drink, his hair is plastered to his head with sweat. He pours half his drink over his head before he notices Anna.  
‘Oh, hey,’ he greets, smiling tiredly. ‘You here alone?’ his eyes do a quick scan of the stands behind them.  
‘No, we’re alone.’ Anna whispers.  
‘No, look, there’s Cas!’ Dean points, and grins. Anna turns around, and Castiel is waving back. She glares at him, but he doesn’t stop.  
Dean focuses back in on Anna. ‘You were saying?’  
‘I’m just reminding you about Saturday.’ she says sweetly.  
Dean nods, smiling widely. ‘Yeah, I can do that. I’ll definitely be there.’ he promises. ‘Just going to get changed.’ he says, and runs off.  
When she turns around, Castiel isn’t in his seat anymore. Bastard.  
~~~  
The decorations are that great mix of scary and fun - not ridiculous, but not too spooky either. Anna is throughly impressed, and she grudingly admits that Gabriel mixed the punch quite well. She’s surprised that it even got mixed, considering the amount of kissing going on in the kitchen during pre-party preparations. Honestly, how Sam didn’t have a constant crick in his neck would remain one of the greatest wonders of the universe.  
Dean was a little late, but Anna was waiting at the door when he came through. Dean’s dressed as a cowboy, right down to the boots.  
‘Hey Dean,’ Anna says. ‘You look really good.’  
Dean’s bouncing on his toes and fidgeting with the pockets of his poncho. Anna thinks he must just be worried about asking her out. ‘Thanks Anna.’ His eyes flit around the room. Probably looking for the beer.  
‘Go find some liquid courage.’ Anna suggests. ‘Get settled, I’ll be over later.’  
Dean nods distractedly, and makes a beeline for the red beer cups.  
Anna socialises like there’s no tommorrow. She does it every day, really, but parties are her style. She laughs at the boys’ stupid jokes, and she compliments the girls on their slutty costumes. She dances with people who ask her to, and sneers at those who don’t. People love her. She’s Anna Milton, how could they not?  
Dean’s still looking nervously around the room, looking far too young for someone who’s 18 and about to graduate. Anna thinks it’s odd, really - Dean doesn’t do the rounds quite as much as she does, of course, but he’s asked out pretty girls before - Lisa Braeden and Cassie Robinson weren’t unnattractive girls; Dean really shouldn’t be worried.  
But he’s thumbing at the rim of his beer cup, crinkling the plastic under his fingers, and his eyes are unusually wide. Anna decides to put him out of his misery.  
‘Hey Dean,’ Anna greets, leaning against the wall. ‘How are you enjoying the party?’  
Dean nods, and visibly tries to relax. ‘Hey Anna! Is… uhm, is Cas here?’  
‘Yeah, with Sam and Gabriel, in the kitchen.’ she replies.  
Dean grins. ‘Thanks,’ he says, and peels off the wall.  
Anna is confused, but she continues to socialise. Dean will come to her in her own time.  
About an hour later, Gabriel taps her on the shoulder. He’s still glued to Sam’s side, and they’re wearing matching smirks. Anna swears Gabriel has gotten more annoying now that he’s dating Sam.  
‘Yes, brother?’ she asks, playing her disinterest for all she’s got.  
Gabriel smiles at her fakely. ‘You might be interested in what’s happening in the kitchen.’  
Anna glares at him, but goes anyway. Gabriel may be annyoing, but he know when to draw a crowd.  
Castiel is perched up on the counter, and Dean is standing next to him, looking up at the other boy.  
‘-and she leans on my car. No-one leans on my car, Cas. Even I don’t lean on my car.’  
Castiel laughs quietly. ‘It’s a nice car, Dean.’  
Dean grins, agreement obvious. ‘Isn’t she?’  
It’s quiet for a moment.  
‘I don’t know much about cars.’ Castiel confesses, watching his feet swing over the floor.  
‘I’ll teach you, then.’ Dean says, and it sounds like a promise.  
Castiel smiles like Anna has never seen him smile.  
She hates it.  
‘Listen, Cas,’ Dean says, and he’s fidgeting again. ‘You’re a pretty cool guy, and-’ no, no, no, this can’t be happening. ‘I was wondering if you’d like to go out with me?’  
Castiel looks confused. Anna is furious. ‘Like, on a date?’ he asks tentatively.  
Dean’s face breaks into a smile. ‘Yeah, if you like.’  
Castiel nods, and the new, stupid smile is back again. ‘Yeah, I wo-’  
‘No!’ Anna shrieks angrily, bursting into the kitchen. ‘No, Castiel, you can’t!’  
Dean jumps a little, shocked at her sudden entrance. ‘Anna, what the fuck?’  
Anna isn’t paying attention to Dean. She’s focused solely on her brother.  
‘Castiel,’ she seethes, ‘I’ve worked for this, okay? And you can’t take it away from me. I’ve earned it, and you haven’t.’  
Castiel smirks cockily. ‘You don’t earn people, Anna.’ he tells her. ‘You don’t own them, and you definitely don’t deserve them.’  
‘I-’ she begins, but Castiel cuts in.  
‘No, Anna.’ He is so calm in his explanation. ‘Go back to your party, sister. Dean and I are going to go upstairs, and you are going to leave us alone.’  
Anna is about to fight it, but something in Castiel’s expression stops her.  
‘I hope you’re happy!’ she spits at their retreating figures.  
She can hear Castiel snort in amusement, and he plasters himself to Dean’s side. ‘I most definitely am!’  
~~~  
 _‘Winchester boys are dumbasses. Gabriel can attest to this, as he is dating one, and in some kind of respect-friendship limbo with the other._  
 _Milton boys are dumbasses, too. Sam can attest to this, as he is dating one, and he is an intellectual solemate or something to the other._  
 _Winchester boys and Milton boys are stupid and stubborn and passionate. They are infuriating and annoying and so emotions blind it isn’t funny._  
 _But Gabriel knows it, and Sam knows it, and hell, Anna probably knows it, but Dean and Cas belong together, and a trip to hell and back wouldn’t break them apart.’_  
‘Chuck, that’s a stupid ending. No-one’s going to believe I wrote that.’ Gabriel complain from where he’s sprawled over the chaise lounge, getting dorito crumbs on his tux.  
‘Well you wanted a good speech.’ the other man grumbles.  
‘I wanted a best man’s speech, not a mother of the damn bride's.’  
Chuck huffs out a laugh. ‘There is no mother of the bride. There’s no bride.’  
Gabriel casts a disbelieving glance at his friend.  
‘What?’ Chuck asks, feigning confusion.  
Gabriel snorts. ‘Please, Dean is totally the bride.’


End file.
